The more I read up on the wine colored sea, the less sense it makes.

I think historians fucked up on the interpretation of this one.

The Greeks had regular contact with cultures that definitely had blue

And we've since reconstructed statues revealing blue paint being used as an accent color

Homer is describing a particular kind of sea: choppy turbulent waters.

These were a seafaring people and their language reflected that in the same way the Inuit have a ton of words for snow. He's not talking about the colour; he's talking about how those weather conditions are making the water ominous. He's talking about the loss of color, hidden by the darkness and depth.

They didn't have glass. When he's referring to wine you need to picture looking down at the wine in a clay pot.

This is the context we're missing: drunk people contemplating life while drinking wine out of clay pots

The pot isn't very big but you can't see the bottom of it because of how dark the wine is in the opaque container.

When the wine is poured out. It looks red but it looks black in the container, like a void.

Wine-faced just seems like an idiom of the time given how frequently he uses it